Villa vacation rentals in Montauk

Southampton Village Dream Walk to Beach & SAmbrose

Southampton Village Dream Two blocks from Main Street and Sant Ambroeus, and a short walk to the beach, this 7+ bedroom, 6 bath home has all modern conveniences in a beautifully landscaped private compound. Northstar is one of the original Southampton Village houses, over 350-year-old, rebuilt from the ground up, completely modernized and in pristine condition. This home delivers the perfect American dream summer vacation. IMPORTANT: Please read the guidelines and rules below before booking:

TREETOPS! An upscale, unique 5 bdrm home with POOL

TREETOPS is a 4850 square ft 5 bedroom Mid century Modern perched on an outcropping of granite cliffs, surrounded by 2 acres of beautiful forest. *Property not suitable for children under 8 years old* Stroll along the loop trail in our woods, sit in the garden, have a fire in the fire pit, or relax and get some sun by the marine-blue, stone-decked pool! Birdwatching, breakfast, and evening cocktails are best on the spacious wrap-around deck. Hiking is just steps away at "Westwoods Trailhead".

Just renovated Southampton retreat w/ heated pool

JUST RENOVATED! INQUIRE ABOUT MONTHLY RENTALS! Come and enjoy with family and friends your own beautiful house in Southampton. 5-minute drive to Cooper’s Beach and to Southampton Village. Enjoy beautiful ocean beaches, have brunch in the Village, swim in your 32’ heated salt water pool, enjoy a BBQ on your patio under the shadow of a Japanese Maple, indulge in a quiet evening with a book by the fireplace, or take advantage of the home office while your family & friends enjoy the property.

Picturesque 5-bedroom Hamptons villa with pool

Relax with the whole family at this peaceful place to stay. Go for a swim in the 20’ x 40’ heated pool or enjoy the scenic garden and woods while lounging in the outdoor living room. Grill some burgers or make s’mores over the fire pit. Centrally located. 6 min. drive to LIRR and Hampton Jitney and minutes to I-495. 2 mins. to bay beaches and 10 mins. to ocean beaches. 10 mins. to Southampton Village. 20 mins. to the wineries. Explore all the Hamptons have to offer and more!

Stylish Beauty with Tennis

30% OFF for July 11-25th Peace and quiet awaits in this stylish modern house on the village fringe. Featuring a first floor Master suite with spa-style master bath, flatscreen TV and direct access to the pool and outdoor shower. The double height, 600 sqft great room is open towards the kitchen and perfect for entertaining. It is equipped with a stunning 82'' flatscreen TV. The south facing deck and heated pool (MD through September) overlook a 6 acre nature reserve.

Luxury Estate-Heated Pool, Fire Pit, Hot Tub

Escape to a private 1.5-acre East Hampton retreat with an Olympic-size pool, hot tub, pool-side gazebo, wrap-around porch, and secluded fire pit under the trees. This stylish 3BR home features a finished basement with ping pong and TV, a garage gym, and modern designer touches throughout. Just minutes from private beaches and both Amagansett and East Hampton village, it’s perfect for families, friends, or couples seeking luxury, privacy, and space to relax or entertain.

Luxe| Pool | GOLF Sim|HotTub|Movie|Arcade|firepit

Insta: @staywithhamptonsmama PINKWOOD PLAYHOUSE is the perfect spot for your Hamptons stay, offering elevated design and relaxed luxury with laid back beach vibes. Perfect for families or couples. This stylish and serene home features 4 bedrooms, 2.5 bathrooms, a fully equipped kitchen, soaring ceilings and an open floorplan. Bring the outdoors in with oversized windows and over 1000 square feet of deck space overlooking the gorgeous pool.

Luxe| Pool|Game Room |Outdoor Movie|HotTub|Firepit

SERENITY AT SHOREWOOD Luxurious Newly Renovated Mid Century Modern Home in East Hampton with Beach Car! Peaceful and stylish with three bedrooms, 3 1/2 baths, spectacular great room, huge deck, heated pool and more, less than four miles to the heart of East Hampton Village, world renowned for its restaurants, shopping and ocean beaches. A designer-curated architectural gem! Kick back and relax in this calm, stylish space.

balcony entrance to ensuite room with king bed +

Take it easy at this private beachfront. wake up to the sound of the waves and birds signing. 12 min from quaint town of Greenport. your room is in the back of my house, up the stairs to balcony entrance facing the ocean. your only neighbors are the seagulls. park in the driveway or pull you car right up on the lawn + sandy dune, stairs down to my private pebble beachfront. lots of waterfront dining.